“I just have always been one of those people who wanted to travel the world,” Kelly told the Friday afternoon crowd at the Inc. Founders House at SXSW in Austin, Texas. “When you spin a globe, put your finger on it, and you’re like, ‘I want to go to Mongolia’—I still do that.”
His obsession with points dates back to the mid-1990s, when his well-traveled father put young Brian in charge of figuring out the best way to use those points for family trips. “It brought our family together,” said Kelly, now 42. “That little bit of joy I experienced was the seed that allowed me to recognize I didn’t want to spend my life at a cubicle in corporate America. But never in a million years did I think it would grow to what it is today.”
After graduating from the University of Pittsburgh, Kelly was hired by Morgan Stanley, where he earned $70,000 a year and a reputation among colleagues for getting the biggest bang out of unused points. “Everyone had points, but no one knew how to use them,” Kelly said. “Airline websites were broken. So I thought, let me be the conduit to help people.”
He started The Points Guy blog in 2010 as a side hustle, charging clients a flat fee of $50 for transforming points into travel packages. “By the spring of 2011, I was making maybe 1,000 bucks a month,” Kelly said. That’s when a college friend who worked at an affiliate marketing company called LinkShare offered to teach him how to earn commissions by promoting another company’s products or services.
“I met with him that day in Times Square and it changed my life,” Kelly claimed. “That’s when my real entrepreneurial spirit started going.”
In his first six months, The Points Guy earned $1 million off his newfound affinity for affiliates. A year later, in 2012, he sold the company to Bankrate Inc. for $28 million. “I took the money and ran,” Kelly said.